In this episode of The Insurance Technology Podcast, Reid chats with Bradley Flowers, founder of Portal Insurance and co-host of the Insurance Guys Podcast, to explore how family influences, personal struggles, and triumphs paved the way for a successful career.

Grab a cup of coffee, sit back, and listen as they unravel the challenges of business ownership and the beauty of building meaningful relationships along the way.

Episode Highlights

• Rural roots in Atmore, Alabama – known for its casino and high-security prison (0:55)
• Getting progressively safer with hobbies, from bull riding to skateboarding to golf (5:22)
• A near-death experience that had nothing to do with bull riding (14:00)
• Starting out in insurance to have time for golf (16:37)
• Bradley’s biggest regret…it might surprise you (18:47)
• Starting an agency and creating the Insurance Guys Podcast (37:46)

In this episode of The Insurance Technology Podcast, Reid chats with Jack Ramsey, the vice president of agent channels at NEXT Insurance, to dive into Jack’s life journey – from his humble beginnings as a shy kid in a small town to his pivotal role at NEXT Insurance.

Tune in to hear how Jack broke through his shyness to create an impact in the insurance industry for a fully digital carrier and is giving back through mentorship and his passion for disaster relief, including the disaster that recently impacted his hometown.

Episode Highlights

• Big family, small town (00:45)
• Turning shy-kid experiences into mentorship opportunities (5:36)
• From door-to-door greeting card salesperson to insurance leader (13:43)
• Waking up excited to represent something different that agents are looking for (23:53)
• The growing talent gap in insurance (35:48)
• A heart for giving back to youth and supporting disaster relief (52:55)

In this episode of The Insurance Technology Podcast, Reid chats with Leticia Trevino, COO at Heffernan Insurance Brokers, to discuss Leticia’s remarkable story, from growing up in the San Francisco Bay Area to a thriving 24-year career at Heffernan.

Tune in to dive into the intricacies of the insurance technology landscape, the challenges and triumphs of leading a major organization, and the importance of staying connected to one's culture and values amidst it all.

Episode Highlights

· Music, culture, and connection (2:30)

· Starting out as a claims adjuster (3:35)

· Targeting Latino markets (7:45)

· Finding satisfaction in team building (9:45)

· The “golden record” (20:47)

· Success equals having a body of work you’re proud of (42:40)

· Setting up the Poder in Action fund for Latina females (44:21)

In this episode of The Insurance Technology Podcast, Reid chats with Adam Denninger, global industry lead for insurance at Capgemini, to discuss everything from musical interests and fighter jet dreams to an appreciation for history and a passion for insurtech.

Tune in to hear about Adam’s dream of going into flight as a fighter jet pilot in the US Air Force evolved into entering the world of insurtech – you won’t want to miss his insights and stories.

Episode Highlights

• From fighter jet dreams to insurance impact (1:43)
• A taste of modern family life and historical interests (2:20)
• Entering insurance at The Hartford, from intern to director (13:56)
• Being a newbie at Capgemini (24:34)
• The right place, the right time, the right data (28:19)
• Leading without fear and being ready to work (1:03:03)
• Doing the right thing (1:09:24)

In this episode of The Insurance Technology Podcast, Reid chats with Send Chief People Officer Pat Caldwell about his early lessons in leadership, work ethic, acceptance and culture that influenced his career trajectory.

Tune in to hear how Pat’s aspirations evolved, from wanting to become a paramedic to going to law school and eventually sending off his good startup culture vibes within the HR insurtech space for an underwriting platform.

Episode Highlights

• Documenting culture and leadership tips as an author (1:08)
• Venturing into insurtech HR at Send (1:11)
• Giving back, realizing work is not your identity (1:27)
• Reminiscing on first-job lessons and “vintage” video stores (12:56)
• Starting in HR at a large Australian mining company (24:09)
• Leaving for London and entrepreneurial dreams (33:27)

In this episode of The Insurance Technology Podcast, co-host Christen Kelley puts Reid in the hot seat to look back at a summer packed with fun and zoom ahead to a season brimming with industry events.

Tune in to hear about Reid’s upcoming work travel adventures and learn about some of the latest trends and news, including the buzz around the Applied Systems/Planck acquisition.

Episode Highlights

• Embracing the summer vibes (00:30)
• Nashville bound for Ivans Connect & Applied Net (3:20)
• Taking center stage as panel moderator at IndieTech (8:35)
• Mingling with C-suite executives at CIAB (12:32)
• Sparking industry-wide connections at ITC (15:19)
• Elevating the AI game with Planck (26:44)

In this episode of The Insurance Technology Podcast, Reid chats with Jason Cass, managing partner of the Insurance Alliance and founder of the Insurance Podcast Network, to share Jason’s story of entrepreneurship that started at an early age on a business venture to milk cows and has led to being a successful insurance entrepreneur.

Get ready for these two podcast hosts and insurance gurus to discuss the rewards of working in the industry and the importance of connectivity. You’ll also discover how to find what Jason calls “tuxedo moments” to sail into success.

Episode Highlights

• An ambitious spirit that started with milking cows (5:22)
• Tuxedo moments and how being different matters (10:01)
• Leading by listening and putting people first (29:42)
• Sailing into success (30:42)
• Giving back, seeing a need and trying to fix it (32:40)
• A love for building things, boating, animals and dive bars (38:15)

In this episode of The Insurance Technology Podcast, Reid chats with Dr. Douglas Brackmann, author and psychologist, for a deep conversation about neurodivergence related to being what Dr. Doug calls “driven.”

Tune in to hear how Doug self-identified as neurodivergent and driven at a young age, and how seeing a psychologist drove him to inspire others to put their soul in the driver’s seat.

Episode Highlights

• Neurodivergence and imposter syndrome (14:30)
• The “driven” trait to thrive in chaos (18:39)
• The hunter-farmer theory (21:43)